Light‐Induced [2 + 2] Cycloaddition of 2‐Morpholinoacrylonitrile to 1‐Naphthalenecarbonitrile

Düpp, Dietrich; Erian, A. W.; Henkel, Gerald

doi:10.1002/cber.19931260132

Cited by 18 publications

(8 citation statements)

References 30 publications

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“…Our previous finding that 1-naphthonitrile (5), when excited in the presence of 2, does not give rise to any 1,4-adduct, instead the two cyclobutanaphthalenes 6 and 7 were formed, 12 is in analogy to related cases in the literature 10,11 (Scheme 2). …”

Section: Methodssupporting

confidence: 53%

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Döpp¹,

Kruse²,

Erian³

et al. 2013

Arkivoc

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2-(Cycloamino)propenenitriles H 2 C=C(CN)N(CH 2 ) n (n = 4, 5, 6, 7) are added to triplet π,π*-excited 1-acetonaphthone forming 8b-acetyl-2-(cycloamino)-1,2,2a,8b-tetrahydrocyclobuta-[a]naphthalene-2-carbonitriles as well as 1-acetyl-9-(cycloamino)-1,4-dihydro-1,4-ethanonaphthalene-9-carbonitriles. Regio-and stereoselectivity of the photocycloadditions and the special role of the cyclobuta[a]naphthalene adducts in the initial stage of the photoadditions are discussed.

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Section: Methodssupporting

confidence: 53%

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Döpp¹,

Kruse²,

Erian³

et al. 2013

Arkivoc

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“…63,64 In the same study, the intramolecular mode was shown to also give cycloadduct isomers 81 and 82, in a 20:1 ratio (unfortunately, no chemical yield was provided) (Scheme 23). Dopp et al 65 studied the reaction of cyanonaphthalene with 1,1-disubstituted olefins. Monosubstituted naphthalenes also underwent intramolecular cycloaddition with enol ethers, but the position of the tether had a strong influence on reactivity.…”

Section: Ortho Cycloaddition With Polycyclic Aromaticsmentioning

confidence: 81%

“…Dopp et al 65 studied the reaction of cyanonaphthalene with 1,1-disubstituted olefins. Monosubstituted naphthalenes also underwent intramolecular cycloaddition with enol ethers, but the 66 Depending on the substituent, various ratios of ortho and para products were obtained, and a triplet biradical mechanism was proposed.…”

Section: Ortho Cycloaddition With Polycyclic Aromaticsmentioning

confidence: 99%

Arene–Alkene Cycloaddition

2016

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Cycloadditions are among the most efficient chemical processes, combining atom economy, stereospecificity, and the ability to generate molecular complexity in a single step. Aromatic rings would in principle be ideal reaction partners, as they contain, at least from the topological point of view, both olefinic and diene subunits; however, the stability of the conjugated aromatic system would be broken by cycloaddition reactions, which are therefore rarely applied, because kinetics and thermodynamics hinder the process. From that aspect, photochemical activation opens interesting perspectives, as one can selectively provide excess energy to one of the reactants but not to the product, thus preventing thermal back reaction. Indeed, aromatic rings show a rich photochemistry, ranging from isomerizations, substitutions, and additions to cycloadditions. In this review, we will focus on cycloadditions, covering literature from early observations up to the present.

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“…Reversible [2 + 2] photocycloaddition leading to 99 was observed. 82 Independently, the biradical intermediate 100 was formed, also in a reversible photochemical reaction. 83 Only the latter intermediate leads to the formation of stable final products.…”

Section: Photocycloadditions With Condensed Aromatic Compoundsmentioning

confidence: 99%

“…In the case of R = 2,5-di t Bu, the corresponding compound 79 is formed in high yields and no side product was detected. Products 80 are formed by an initial [2 + 4] cycloaddition involving the carbonyl π-bond of the aldehyde function and one π-bond of the aromatic moiety (82). It must, however, be pointed out that these reactions are most probably not concerted.…”

Section: The [2 + 3] or Meta Photocycloadditionmentioning

confidence: 99%

Photochemical reactions of aromatic compounds and the concept of the photon as a traceless reagent

Hoffmann

2012

Photochem Photobiol Sci

123

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Electronic excitation significantly changes the reactivity of chemical compounds. Compared to ground state reactions, photochemical reactions considerably enlarge the application spectrum of a particular functional group in organic synthesis. Multistep syntheses may be simplified and perspectives for target oriented synthesis (TOS) and diversity oriented synthesis (DOS) are developed. New compound families become available or may be obtained more easily. In contrast to common chemical reagents, photons don't generate side products resulting from the transformation of a chemical reagent. Therefore, they are considered as a traceless reagent. Consequently, photochemical reactions play a central role in the methodology of sustainable chemistry. This aspect has been recognized since the beginning of the 20th century. As with many other photochemical transformations, photochemical reactions of aromatic, benzene-like compounds illustrate well the advantages in this context. Photochemical cycloadditions of aromatic compounds have been investigated for a long time. Currently, they are applied in various fields of organic synthesis. They are also studied in supramolecular structures. The phenomena of reactivity and stereoselectivity are investigated. During recent years, photochemical electron transfer mediated reactions are particularly focused. Such transformations have likewise been performed with aromatic compounds. Reactivity and selectivity as well as application to organic synthesis are studied.

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Light‐Induced [2 + 2] Cycloaddition of 2‐Morpholinoacrylonitrile to 1‐Naphthalenecarbonitrile

Cited by 18 publications

References 30 publications

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Arene–Alkene Cycloaddition

Photochemical reactions of aromatic compounds and the concept of the photon as a traceless reagent

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